oxprenolol

Absorption

Oral bioavailability is 20-70%.

Toxicity

Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.

Description

Oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in the division for drug synthesis. Epichlorhydrin was also used for the production of both propranolol and oxprenolol.

Originator

Trasicor,Ciba Geigy ,Italy,1970

The Uses of oxprenolol

Oxprenolol is a free base of Oxprenolol Hydrochloride(O870500) which is a β-Adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.

The Uses of oxprenolol

Vasodilator(coronary).

Indications

Used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.

Background

A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.

Definition

ChEBI: 1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)-2-propanol is an aromatic ether.

Manufacturing Process

75 grams of pyrocatechol monoallyl ether, 75 grams of epichlorohydrin, 75 grams of potassium carbonate and 400 ml of acetone are stirred and heated at the boil for 12 hours. The potassium carbonate is then filtered off. The solvent is distilled off in a water-jet vacuum. The residual oil is dissolved in ether and agitated with 2 N sodium hydroxide solution. The ether is separated, dried and distilled off. The residue is distilled in a water-jet vacuum. 3-(ortho-allyloxy-phenoxy)-1,2-epoxypropane passes over at 145° to 157°C under 11 mm Hg pressure. A solution of 15 grams of 3-(ortho-allyloxyphenoxy)-1,2-epoxypropane and 15 grams of isopropylamine in 20 ml of ethanol is refluxed for 4 hours. The excess amine and the alcohol are then distilled off under vacuum, to leave 1-isopropylamino-2-hydroxy-3-(orthoallyloxy-phenoxy)-propane which melts at 75° to 80°C after recrystallization from hexane.

brand name

Trasicor (Novartis).

Therapeutic Function

Antiarrhythmic

Contact allergens

The beta-blocker oxprenolol induced contact dermatitis in a worker at a pharmaceutical plant, in a division for drug synthesis. Epichlorhydrin was also used for the production of drugs propranolol and oxprenolol.

Pharmacokinetics

Oxprenolol is a non-selective beta blocker with some intrinsic sympathomimetic activity. Oxprenolol is a lipophilic molecule and hence, it is able to cross the blood-brain barrier. As such, it is associated with a higher incidence of CNS-related side effects than hydrophilic ligands such as atenolol, sotalol and nadolol. Oxprenolol is an potent beta-blocker and should not be administered to asthmatics because it can cause irreversible airway failure and inflammation.

Metabolism

Hepatic.